1547-15-5

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE is used as a potential drug candidate for its potential anti-inflammatory properties, offering a new avenue for the treatment of inflammatory conditions.
3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE is used as a potential analgesic agent, providing pain relief through its possible interaction with pain signaling pathways.
3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE is used as a potential anticonvulsant, potentially managing seizures and epilepsy by modulating neuronal excitability.
3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE is used as a potential anticancer agent, targeting various types of cancer cells and potentially enhancing the efficacy of conventional chemotherapy.
Further research is necessary to explore the full range of applications and to develop appropriate drug delivery systems to optimize the therapeutic potential of 3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE.

InChI:InChI=1/C14H9FN2OS/c15-9-5-7-10(8-6-9)17-13(18)11-3-1-2-4-12(11)16-14(17)19/h1-8H,(H,16,19)

Upstream product

• 134-20-3 2-carbomethoxyaniline 
• 4314-19-6 bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione 
• 371-40-4 4-fluoroaniline 
• 33692-68-1 N-(4-fluorophenyl)methyl dithiocarbamic acid 
• 118-92-3 anthranilic acid 
• 1544-68-9 4-fluorophenyl isothiocyanate 
• 118-48-9 isatoic anhydride 
• 16332-89-1 3-(4-Fluorophenyl)quinazoline-2,4(1H,3H)-dione 
• 75-15-0 carbon disulfide 
• 216502-06-6 2-amino-N-(4'-fluorophenyl)benzamide 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 16024-82-1 methyl 2-isothiocyanatobenzoate 
• 19182-34-4 ammonium p-fluorophenyldithiocarbamate 

Downstream Products

• 1298113-86-6 C₁₆H₉FN₄O₃ 
• 67811-51-2 4-(4-fluorophenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 66679-71-8 2-hydrazino-3-(4-fluorophenyl)quinazolin-4(3H)-one 
• 1017084-43-3 C₂₃H₁₇FN₂O₂S 
• 443347-74-8 C₂₂H₁₄ClFN₂O₂S 

Relevant academic research and scientific papers

Design, synthesis, and anti-inflammatory activity of novel quinazolines

Several new fluorinated quinazolinone derivatives were prepared and evaluated for in vitro anti-inflammatory activity. The molecular modelling study was performed for compounds 4, 8, 9, 10 and 13. The tested compounds showed strong interactions at the COX

Design, synthesis, biological evaluation, and molecular docking study of thioxo-2,3-dihydroquinazolinone derivative as tyrosinase inhibitors

Tyrosinase is known to be a key enzyme in melanogenesis and hyperpigmentation. In this study, a series of thioxo-dihydroquinazolinone compounds were designed and synthesized as tyrosinase inhibitors. Among the investigated compounds, 4m demonstrated the best inhibitory activity with an IC50 value of 15.48 μM compared to kojic acid as a positive control with IC50 value of 9.30 μM. In kinetic evaluation against tyrosinase, 4m depicted a mixed inhibition pattern. Additionally, antioxidant evaluations exhibited moderate to weak potency in 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The detailed interactions and binding mode toward tyrosinase of the most potent derivative were explicated by molecular docking study. Moreover, the computer-aided drug-likeness and pharmacokinetic studies were also carried out.

Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives

A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.

Divergent 2-Chloroquinazolin-4(3H)-one Rearrangement: Twisted-Cyclic Guanidine Formation or Ring-Fused N-Acylguanidines via a Domino Process

A highly efficient 2-chloroquinazolin-4(3H)-one rearrangement was developed that predictably generates either twisted-cyclic or ring-fused guanidines in a single operation, depending on the presence of a primary versus secondary amine in the accompanying diamine reagent. Exclusive formation of twisted-cyclic guanidines results from pairing 2-chloroquinazolinones with secondary diamines. Use of primary amine-containing diamines permits a domino quinazolinone rearrangement/intramolecular cyclization, gated through (E)-twisted-cyclic guanidines, to afford ring-fused N-acylguanidines. This scalable, structurally tolerant transformation generated 55 guanidines and delivered twisted-cyclic guanidines with robust plasma stability and an abbreviated total synthesis of an antitumor ring-fused guanidine (4 steps, 55 % yield).

CuBr-catalysed one-pot multicomponent synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives

A novel methodology is presented for the synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives based on an efficient tandem multicomponent reaction using copper bromide as catalyst. This methodology is based on the multicomponent one-pot reaction of methyl 2-bromobenzoate, phenylisothiocyanate derivatives and sodium azide in the presence of copper bromide and l-proline under basic conditions. To show the generality of the method, various phenylisothiocyanates bearing electron-donating or electron-withdrawing functionalities were used and the desired products were obtained in high isolated yields.

Design, synthesis and antimicrobial activities of 1-(4-oxo-3-(4-fluorophenyl)-3H-quinazolin-2-yl)-4-(substituted) thiosemicarbazide derivatives

A new series of 1-(4-oxo-3-(4-fluorophenyl)-3H-quinazolin-2-yl)-4-(substituted) thiosemicarbazides (AR1-AR10) were obtained by the reaction of 2-hydrazino-3-(4-fluorophenyl) quinazolin-4(3H)-one (6) with different dithiocarbamic acid methyl ester derivatives. The key intermediate 3-(4-fluorophenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one (4) was obtained by reacting 4-fluoroaniline (1) with carbon disulphide and sodium hydroxide in dimethyl sulphoxide to give sodium dithiocarbamate, which was methylated with dimethyl sulfate to yield the dithiocarbamic acid methyl ester (2) and condensed with methyl anthranilate (3) in ethanol yielded the desired compound (4) via the thiourea intermediate. The SH group of compound (4) was methylated for the favorable nucleophilic displacement reaction with hydrazine hydrate, which afford 2-hydrazino-3-(4-fluorophenyl)-3H-quinazolin-4-one (6). All synthesized compounds (AR1-AR10) were also screened for their antimicrobial activity against selective gram positive and gram negative by agar dilution method. In the present study compounds AR8 and AR9 were emerged as the most active compounds of the series.

A convenient and efficient synthesis of 2-thioxoquinazolinone derivatives via microwave irradiation

The synthesis of 2-thioxoquinazolinone derivatives was achieved by condensation of isatoic anhydride, primary amine, and carbon disulfide under microwave irradiation. This convenient and efficient method affords the desired products with good to excellent yields. Satisfactory infrared spectroscopy, 1H NMR, and high-resolution mass spectrometry (electrospray ionization) spectra were obtained for all compounds described.

Synthesis and Anticonvulsant Activity Evaluation of 4-Phenyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one and Its Derivatives

A series of 4-(substituted-phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones (6a-x) with triazole and other heterocyclic substituents (7-14) were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity by maximal electroshock (MES) and rotarod neurotoxicity tests. Among the compounds studied, 6o and 6q showed wide margins of safety with protective indices (PIs) that were much higher than those of currently used drugs (PI6o > 25.5, PI6q > 26.0). Compounds 6o and 6q showed significant oral activity against MES-induced seizures in mice, with ED50 values of 88.02 and 94.6 mg/kg, respectively. The two compounds were also found to have potent activity against seizures that were induced by pentylenetetrazole and bicuculline. A series of 4-(substituted-phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones with triazole and other heterocyclic substituents were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity using maximal electroshock and rotarod neurotoxicity tests.

Design, synthesis and anticonvulsant activity of some newer 3H-quinazolin-4-one derivatives

In the present investigation, a series of 2-[2-(aryl)-2-oxo-ethylsulfanyl]- 3-(aryl/propyl)-3H-quinazolin-4-ones have been synthesized and tested for their potential against seizures in mice. All the newly synthesized compounds show moderate to high protection against 6 Hz partial seizure with compound 2b, 2-(2-oxo-2-p-tolyl-ethylsulfanyl)-3-phenyl-3H-quinazolin-4-one emerging as the most active anticonvulsant agent endowed with neuroprotective effect against NMDA and kainate induced excitotoxicity. The results of whole brain GABA assay indicates that the seizure protective activity of 2b can be either due to the increased brain GABA level or due to neuroprotective action.

Facile route for novel quinazolinone-fused azauracils through cyclodesulfurization of thioquinazolinones

An efficient, novel, short, and high-yielding one-pot protocol for the synthesis of diverse quinazolinone-fused azauracil heterocycles through cyclodesulfurization and intramolecular cyclization of thioquinazolinone using silver cyanate is described. Georg Thieme Verlag Stuttgart.